Ammonia → HCID 89650994, compound

HRID 515939Notes

Reaction equation

C([O:9][C@H:10]1[C@:14]([F:16])([CH3:15])[C@H:13]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[O:12][C@@:11]1([F:34])[CH2:25]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N.C[OH:37]>>[F:16][C@:14]1([CH3:15])[C@H:10]([OH:9])[C@@:11]([F:34])([CH2:25][OH:37])[O:12][C@H:13]1[N:17]1[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]1=[O:24]

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol2×

HCID 131733327HCID 131733327, compound

Product 1

HCID 89650994HCID 89650994, compoundYield 38%

Procedure

Chiral (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,4-difluor-O-2-benzoylmethyl-4-methyl-tetrahydrofuran-3-yl benzoate (0.34 g, 0.7 mmol) was dissolved into methanol, and a solution of ammonia in methanol (7 N, 20 mL) was added. The reaction mixture was stirred at room temperature for overnight. The mixture was concentrated, and the residue was purified by silica gel column chromatography (DCM:MeOH=20:1) and pre-HPLC to afford the title compound as a white solid (0.074 g, 38%).

Workup

concentrationThe mixture was concentrated
customthe residue was purified by silica gel column chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-30de34eda843420395b4a164d783dc16
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108999B2

Reaction notes

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